NPASS Compound

Structure

CID36181 OpenBabel06191715362D 29 31 0 0 0 0 0 0 0 0999 V2000 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 8 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 15 17 1 0 0 0 0 16 22 1 0 0 0 0 16 24 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.16
Volume:	415.577
LogP:	6.184
LogD:	3.684
LogS:	-4.093
# Rotatable Bonds:	6
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	2.737
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.793
MDCK Permeability:	1.60757772391662e-05
Pgp-inhibitor:	0.702
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.557
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	97.72695922851562%
Volume Distribution (VD):	0.459
Pgp-substrate:	2.5235581398010254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.675
CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.838
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.281
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	7.671
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.833
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.252
Maximum Recommended Daily Dose:	0.082
Skin Sensitization:	0.467
Carcinogencity:	0.193
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.323

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC36181

Natural Product ID:	NPC36181
*Common Name:**	Mammea A/Ac
IUPAC Name:	6-butanoyl-5,7-dihydroxy-8-(3-methylbut-2-enyl)-4-phenylchromen-2-one
Synonyms:
Standard InCHIKey:	NWWAVRDKPXDXSM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H24O5/c1-4-8-18(25)21-22(27)16(12-11-14(2)3)24-20(23(21)28)17(13-19(26)29-24)15-9-6-5-7-10-15/h5-7,9-11,13,27-28H,4,8,12H2,1-3H3
SMILES:	CCCC(=O)c1c(O)c2c(cc(=O)oc2c(c1O)CC=C(C)C)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453876
PubChem CID:	44546137
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4557	Kayea assamica	Species	Calophyllaceae	Eukaryota	flower	Myanmar	n.a.	PMID[18640837]
NPO4557	Kayea assamica	Species	Calophyllaceae	Eukaryota	flowers	Myanmar	n.a.	PMID[18725180]
NPO32974	mammea siamensis	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22831798]
NPO32974	mammea siamensis	Species	Calophyllaceae	Eukaryota	flower	n.a.	n.a.	PMID[23206866]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24211545]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	Urine	n.a.	n.a.	PMID[6330305]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[932730]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20728	Pinus rigida	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17801	Drimia altissima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20728	Pinus rigida	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22008	Artemisia santolinifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20728	Pinus rigida	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17801	Drimia altissima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24343	Dalbergia spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21479	Antiaris africana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4557	Kayea assamica	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	6

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	Cytotoxicity	=	16.0	uM	PMID[508228]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	0.6	%	PMID[508229]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	14.2	%	PMID[508229]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	46.9	%	PMID[508229]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	67.6	%	PMID[508229]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	96.8	%	PMID[508229]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	13000.0	nM	PMID[508229]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC36181 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	1624
0.2-0.3	3969
0.3-0.4	9938
0.4-0.5	8564
0.5-0.6	3858
0.6-0.7	5931
0.7-0.8	4556
0.8-0.85	2196
0.85-0.9	1334
0.9-0.95	297
0.95-1	51

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC196459
0.9927	High Similarity	NPC87609
0.9927	High Similarity	NPC112791
0.9927	High Similarity	NPC470296
0.9927	High Similarity	NPC94794
0.9927	High Similarity	NPC188632
0.9855	High Similarity	NPC1886
0.9855	High Similarity	NPC469935
0.9855	High Similarity	NPC178627
0.9855	High Similarity	NPC196137
0.9784	High Similarity	NPC470322
0.9784	High Similarity	NPC154217
0.9784	High Similarity	NPC57470
0.9784	High Similarity	NPC181388
0.9714	High Similarity	NPC249942
0.9714	High Similarity	NPC140120
0.9714	High Similarity	NPC180477
0.9714	High Similarity	NPC297886
0.9712	High Similarity	NPC469953
0.9645	High Similarity	NPC469933
0.9645	High Similarity	NPC208303
0.9645	High Similarity	NPC161864
0.9635	High Similarity	NPC220062
0.9635	High Similarity	NPC55018
0.9635	High Similarity	NPC217186
0.9635	High Similarity	NPC301217
0.9635	High Similarity	NPC303633
0.9635	High Similarity	NPC53181
0.9635	High Similarity	NPC96565
0.9635	High Similarity	NPC216978
0.9577	High Similarity	NPC469932
0.9577	High Similarity	NPC19238
0.9565	High Similarity	NPC261227
0.9565	High Similarity	NPC241100
0.9565	High Similarity	NPC221173
0.9565	High Similarity	NPC270883
0.9565	High Similarity	NPC159275
0.9565	High Similarity	NPC172986
0.9562	High Similarity	NPC201395
0.951	High Similarity	NPC151973
0.951	High Similarity	NPC474735
0.9496	High Similarity	NPC470555
0.9496	High Similarity	NPC147688
0.9496	High Similarity	NPC205006
0.9496	High Similarity	NPC156590
0.9496	High Similarity	NPC110969
0.9496	High Similarity	NPC118840
0.9496	High Similarity	NPC64908
0.9496	High Similarity	NPC282300
0.9493	High Similarity	NPC78913
0.9493	High Similarity	NPC473209
0.9493	High Similarity	NPC18260
0.9489	High Similarity	NPC131782
0.9489	High Similarity	NPC138047
0.9489	High Similarity	NPC474624
0.9444	High Similarity	NPC290671
0.9441	High Similarity	NPC104236
0.9441	High Similarity	NPC164205
0.9429	High Similarity	NPC226636
0.9429	High Similarity	NPC299080
0.9429	High Similarity	NPC78803
0.9429	High Similarity	NPC266725
0.9429	High Similarity	NPC59739
0.9429	High Similarity	NPC293852
0.9429	High Similarity	NPC214236
0.9429	High Similarity	NPC200694
0.9429	High Similarity	NPC217083
0.9429	High Similarity	NPC11561
0.9429	High Similarity	NPC62840
0.9424	High Similarity	NPC475680
0.9424	High Similarity	NPC305355
0.9424	High Similarity	NPC150522
0.9424	High Similarity	NPC69769
0.9424	High Similarity	NPC235239
0.942	High Similarity	NPC183639
0.942	High Similarity	NPC199458
0.942	High Similarity	NPC470083
0.942	High Similarity	NPC219584
0.9416	High Similarity	NPC13408
0.9366	High Similarity	NPC153758
0.9362	High Similarity	NPC38219
0.9362	High Similarity	NPC219915
0.9362	High Similarity	NPC212932
0.9362	High Similarity	NPC11700
0.9362	High Similarity	NPC293053
0.9362	High Similarity	NPC9117
0.9362	High Similarity	NPC24821
0.9362	High Similarity	NPC190637
0.9357	High Similarity	NPC14871
0.9357	High Similarity	NPC248372
0.9357	High Similarity	NPC103362
0.9357	High Similarity	NPC110038
0.9353	High Similarity	NPC472343
0.9353	High Similarity	NPC241975
0.9353	High Similarity	NPC19476
0.9348	High Similarity	NPC332594
0.931	High Similarity	NPC312549
0.931	High Similarity	NPC209142
0.9296	High Similarity	NPC319752
0.9296	High Similarity	NPC234629
0.9296	High Similarity	NPC326500
0.9296	High Similarity	NPC257236
0.9296	High Similarity	NPC273538
0.9296	High Similarity	NPC278175
0.9296	High Similarity	NPC216538
0.9296	High Similarity	NPC311741
0.9291	High Similarity	NPC10937
0.9291	High Similarity	NPC473042
0.9291	High Similarity	NPC324134
0.9291	High Similarity	NPC64915
0.9291	High Similarity	NPC227579
0.9291	High Similarity	NPC37496
0.9291	High Similarity	NPC324436
0.9291	High Similarity	NPC223500
0.9291	High Similarity	NPC40833
0.9291	High Similarity	NPC265040
0.9291	High Similarity	NPC76338
0.9291	High Similarity	NPC1089
0.9291	High Similarity	NPC177354
0.9291	High Similarity	NPC296917
0.9291	High Similarity	NPC161506
0.9291	High Similarity	NPC32739
0.9291	High Similarity	NPC78
0.9291	High Similarity	NPC66515
0.9291	High Similarity	NPC166482
0.9291	High Similarity	NPC306829
0.9291	High Similarity	NPC194432
0.9291	High Similarity	NPC166934
0.9291	High Similarity	NPC220998
0.9291	High Similarity	NPC125855
0.9291	High Similarity	NPC182852
0.9291	High Similarity	NPC328164
0.9291	High Similarity	NPC107572
0.9291	High Similarity	NPC167624
0.9291	High Similarity	NPC76372
0.9291	High Similarity	NPC228504
0.9291	High Similarity	NPC148757
0.9291	High Similarity	NPC144499
0.9281	High Similarity	NPC248995
0.9281	High Similarity	NPC272844
0.9281	High Similarity	NPC470669
0.9281	High Similarity	NPC254168
0.9281	High Similarity	NPC470668
0.9275	High Similarity	NPC194281
0.9275	High Similarity	NPC47815
0.9275	High Similarity	NPC174999
0.9275	High Similarity	NPC231772
0.9275	High Similarity	NPC473887
0.9275	High Similarity	NPC124784
0.9275	High Similarity	NPC127447
0.9275	High Similarity	NPC29353
0.9275	High Similarity	NPC234133
0.927	High Similarity	NPC103842
0.9252	High Similarity	NPC469934
0.9252	High Similarity	NPC108937
0.9252	High Similarity	NPC279218
0.9231	High Similarity	NPC83357
0.9231	High Similarity	NPC178343
0.9231	High Similarity	NPC67805
0.9231	High Similarity	NPC88964
0.9231	High Similarity	NPC54577
0.9231	High Similarity	NPC267375
0.9231	High Similarity	NPC470647
0.9231	High Similarity	NPC111786
0.9231	High Similarity	NPC220418
0.9231	High Similarity	NPC475052
0.9231	High Similarity	NPC5820
0.9231	High Similarity	NPC142405
0.9231	High Similarity	NPC124729
0.9231	High Similarity	NPC301276
0.9231	High Similarity	NPC306488
0.9231	High Similarity	NPC246948
0.9231	High Similarity	NPC474161
0.9231	High Similarity	NPC214774
0.9231	High Similarity	NPC476088
0.9231	High Similarity	NPC312973
0.9231	High Similarity	NPC195621
0.9231	High Similarity	NPC176229
0.9231	High Similarity	NPC20488
0.9225	High Similarity	NPC75049
0.9225	High Similarity	NPC166138
0.9225	High Similarity	NPC310130
0.9225	High Similarity	NPC107177
0.9225	High Similarity	NPC175504
0.9225	High Similarity	NPC185276
0.9225	High Similarity	NPC77794
0.9225	High Similarity	NPC85162
0.9225	High Similarity	NPC223812
0.9225	High Similarity	NPC214166
0.9225	High Similarity	NPC149026
0.9225	High Similarity	NPC18585
0.9225	High Similarity	NPC143896
0.9225	High Similarity	NPC221432
0.9225	High Similarity	NPC81697
0.9225	High Similarity	NPC257097
0.9225	High Similarity	NPC39329
0.9225	High Similarity	NPC150408
0.9225	High Similarity	NPC169591
0.9225	High Similarity	NPC125894
0.9225	High Similarity	NPC158874

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC36181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	963
0.2-0.3	1526
0.3-0.4	2583
0.4-0.5	1967
0.5-0.6	1192
0.6-0.7	379
0.7-0.8	124
0.8-0.85	41
0.85-0.9	23
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9296	High Similarity	NPD4378	Clinical (unspecified phase)
0.9296	High Similarity	NPD7410	Clinical (unspecified phase)
0.9048	High Similarity	NPD7411	Suspended
0.8936	High Similarity	NPD1552	Clinical (unspecified phase)
0.8936	High Similarity	NPD1550	Clinical (unspecified phase)
0.8874	High Similarity	NPD7075	Discontinued
0.8873	High Similarity	NPD1549	Phase 2
0.8859	High Similarity	NPD6801	Discontinued
0.88	High Similarity	NPD7819	Suspended
0.88	High Similarity	NPD7096	Clinical (unspecified phase)
0.8794	High Similarity	NPD1510	Phase 2
0.8777	High Similarity	NPD1240	Approved
0.875	High Similarity	NPD3750	Approved
0.8732	High Similarity	NPD2796	Approved
0.8699	High Similarity	NPD6799	Approved
0.8681	High Similarity	NPD7421	Clinical (unspecified phase)
0.8681	High Similarity	NPD1243	Approved
0.8675	High Similarity	NPD2393	Clinical (unspecified phase)
0.8652	High Similarity	NPD1607	Approved
0.8618	High Similarity	NPD8443	Clinical (unspecified phase)
0.86	High Similarity	NPD4380	Phase 2
0.8571	High Similarity	NPD1511	Approved
0.8562	High Similarity	NPD7768	Phase 2
0.8535	High Similarity	NPD7852	Clinical (unspecified phase)
0.8506	High Similarity	NPD3749	Approved
0.85	High Similarity	NPD6859	Clinical (unspecified phase)
0.85	High Similarity	NPD2313	Discontinued
0.8483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD6599	Discontinued
0.8456	Intermediate Similarity	NPD1512	Approved
0.8431	Intermediate Similarity	NPD2801	Approved
0.8425	Intermediate Similarity	NPD2800	Approved
0.8406	Intermediate Similarity	NPD1203	Approved
0.8403	Intermediate Similarity	NPD2799	Discontinued
0.8403	Intermediate Similarity	NPD3748	Approved
0.84	Intermediate Similarity	NPD920	Approved
0.8387	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD3817	Phase 2
0.8369	Intermediate Similarity	NPD3268	Approved
0.8366	Intermediate Similarity	NPD1934	Approved
0.8345	Intermediate Similarity	NPD2935	Discontinued
0.8345	Intermediate Similarity	NPD1551	Phase 2
0.8278	Intermediate Similarity	NPD5403	Approved
0.8273	Intermediate Similarity	NPD2797	Approved
0.8267	Intermediate Similarity	NPD2534	Approved
0.8267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD2533	Approved
0.8267	Intermediate Similarity	NPD2532	Approved
0.8264	Intermediate Similarity	NPD6651	Approved
0.8261	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD422	Phase 1
0.8188	Intermediate Similarity	NPD9717	Approved
0.8176	Intermediate Similarity	NPD6232	Discontinued
0.817	Intermediate Similarity	NPD3226	Approved
0.816	Intermediate Similarity	NPD5953	Discontinued
0.8148	Intermediate Similarity	NPD7286	Phase 2
0.8146	Intermediate Similarity	NPD5401	Approved
0.8137	Intermediate Similarity	NPD7473	Discontinued
0.8121	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6959	Discontinued
0.8099	Intermediate Similarity	NPD6832	Phase 2
0.8089	Intermediate Similarity	NPD3882	Suspended
0.8071	Intermediate Similarity	NPD3225	Approved
0.8069	Intermediate Similarity	NPD5124	Phase 1
0.8069	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2346	Discontinued
0.8027	Intermediate Similarity	NPD4308	Phase 3
0.8027	Intermediate Similarity	NPD7033	Discontinued
0.8014	Intermediate Similarity	NPD3267	Approved
0.8014	Intermediate Similarity	NPD3266	Approved
0.7987	Intermediate Similarity	NPD919	Approved
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7963	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6166	Phase 2
0.7963	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7054	Approved
0.7927	Intermediate Similarity	NPD5844	Phase 1
0.7919	Intermediate Similarity	NPD2344	Approved
0.7911	Intermediate Similarity	NPD5402	Approved
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7881	Intermediate Similarity	NPD4628	Phase 3
0.7881	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7074	Phase 3
0.7879	Intermediate Similarity	NPD7472	Approved
0.7862	Intermediate Similarity	NPD1296	Phase 2
0.7844	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2798	Approved
0.7831	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD5494	Approved
0.7785	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.7755	Intermediate Similarity	NPD4307	Phase 2
0.774	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7808	Phase 3
0.7736	Intermediate Similarity	NPD1465	Phase 2
0.7733	Intermediate Similarity	NPD6099	Approved
0.7733	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2309	Approved
0.7698	Intermediate Similarity	NPD1548	Phase 1
0.7688	Intermediate Similarity	NPD4288	Approved
0.7676	Intermediate Similarity	NPD1608	Approved
0.7658	Intermediate Similarity	NPD6585	Discontinued
0.7635	Intermediate Similarity	NPD943	Approved
0.7622	Intermediate Similarity	NPD5710	Approved
0.7622	Intermediate Similarity	NPD5711	Approved
0.7619	Intermediate Similarity	NPD411	Approved
0.7616	Intermediate Similarity	NPD5406	Approved
0.7616	Intermediate Similarity	NPD5405	Approved
0.7616	Intermediate Similarity	NPD5404	Approved
0.7616	Intermediate Similarity	NPD5408	Approved
0.7613	Intermediate Similarity	NPD7390	Discontinued
0.761	Intermediate Similarity	NPD5889	Approved
0.761	Intermediate Similarity	NPD5890	Approved
0.7606	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4908	Phase 1
0.7584	Intermediate Similarity	NPD1933	Approved
0.7584	Intermediate Similarity	NPD447	Suspended
0.7584	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4287	Approved
0.7571	Intermediate Similarity	NPD9545	Approved
0.7554	Intermediate Similarity	NPD9493	Approved
0.7517	Intermediate Similarity	NPD1164	Approved
0.7516	Intermediate Similarity	NPD5049	Phase 3
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD4363	Phase 3
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7468	Intermediate Similarity	NPD2654	Approved
0.7466	Intermediate Similarity	NPD1019	Discontinued
0.7465	Intermediate Similarity	NPD17	Approved
0.7458	Intermediate Similarity	NPD4361	Phase 2
0.7458	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1247	Approved
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4625	Phase 3
0.7431	Intermediate Similarity	NPD1481	Phase 2
0.7419	Intermediate Similarity	NPD7003	Approved
0.741	Intermediate Similarity	NPD7229	Phase 3
0.7391	Intermediate Similarity	NPD5535	Approved
0.7389	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2354	Approved
0.7365	Intermediate Similarity	NPD3926	Phase 2
0.7361	Intermediate Similarity	NPD1535	Discovery
0.7355	Intermediate Similarity	NPD1652	Phase 2
0.7353	Intermediate Similarity	NPD1729	Discontinued
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7324	Intermediate Similarity	NPD1894	Discontinued
0.7321	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3972	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4476	Approved
0.7273	Intermediate Similarity	NPD4477	Approved
0.7248	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7199	Phase 2
0.7241	Intermediate Similarity	NPD1201	Approved
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7235	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6004	Phase 3
0.7226	Intermediate Similarity	NPD6002	Phase 3
0.7226	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2353	Approved
0.7226	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6005	Phase 3
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7188	Intermediate Similarity	NPD6273	Approved
0.7184	Intermediate Similarity	NPD8313	Approved
0.7184	Intermediate Similarity	NPD8312	Approved
0.7181	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.7169	Intermediate Similarity	NPD6971	Discontinued
0.7162	Intermediate Similarity	NPD1470	Approved
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2296	Approved
0.7152	Intermediate Similarity	NPD3887	Approved
0.7151	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7135	Intermediate Similarity	NPD7177	Discontinued
0.7117	Intermediate Similarity	NPD6502	Phase 2
0.7115	Intermediate Similarity	NPD1471	Phase 3
0.7107	Intermediate Similarity	NPD7440	Discontinued
0.7104	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD74	Approved
0.7101	Intermediate Similarity	NPD9266	Approved
0.7095	Intermediate Similarity	NPD1283	Approved
0.7092	Intermediate Similarity	NPD1241	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data